Questlove's Top 50 Hip-Hop Songs of All Time

What makes a great hip-hop song? Ahmir "Questlove" Thompson chooses his favorites.

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DJ Jazzy Jeff and the Fresh Prince,
Michael Ochs Archives/Getty Images45/50

45. DJ Jazzy Jeff and the Fresh Prince, "Summertime" (1991)

The level of wildfire-speed word of mouth this single got in '91 was unbelievable. No one could believe it. I'll describe it the same way Black Thought rang me up on the phone after he first heard it: "It's like he lost all that animated happy flow and did Rakim's 'Paid in Full' flow . . . but better than Rakim!!!" I kinda have to say, this single was the best pop hit Eric B. and Rakim never got to record. For the first time, the Fresh Prince's Clark Kent was given a back seat while Will's Supermanisms took the wheel. This gave you the real view of the streets of Philadelphia.

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